PSS Activations Specialist

The Payment Success Specialist – Activation is a pivotal, high-impact role that shapes the first impression and long-term success of Weave’s payments customers. As a trusted advisor and subject matter expert, you will lead customers through a strategic, white-glove onboarding journey — transforming the activation experience into a catalyst for sustained adoption, revenue growth, and operational transformation.

In this role, you are not simply enabling transactions — you are architecting how new customers integrate payments into their business model from day one. You’ll design activation strategies tailored to each customer’s workflows, train their teams with precision, and guide them through early adoption milestones that lay the foundation for long-term success. Your ability to influence behavior, anticipate challenges, and drive measurable outcomes will directly impact retention, revenue, and customer lifetime value.

This role reports to the Manager of Payment Success

This role is hybrid in office

• Serve as the primary consultant and trusted advisor for new payments customers, delivering a world-class onboarding experience from kickoff to activation.

• Lead comprehensive Payment Success Introduction + Training Calls that go beyond setup — aligning Weave’s capabilities with the customer’s operational goals and success metrics.

• Ensure flawless deployment of hardware, software, and Text-to-Pay workflows
  , guiding customers through best-practice configurations and tailored implementation plans.

• Design activation roadmaps that strategically guide customers toward their first milestones, including completing three transactions with unique customers ,while embedding Weave Payments into daily operations.

• Establish clear activation success criteria and set expectations for adoption, usage, and continued engagement.

• Conduct proactive follow-up engagements with key stakeholders, assessing adoption progress and identifying opportunities for optimization.

• Deliver strategic recommendations to remove barriers, streamline workflows, and maximize payment utilization — positioning Weave as a mission-critical revenue tool.

• Act as a payments SME
  , advising customers on industry best practices, regulatory nuances, and operational strategies that improve financial performance.

• Monitor customer processing volume for six months post-activation
  , using data-driven insights to identify opportunities for increased usage and deeper platform adoption.

• Strategically guide customers toward reaching $5,000 in monthly processing volume — positioning them as Meaningful Volume Customers (MVC) and unlocking the full potential of Weave Payments.

• Partner with internal stakeholders across Customer Success, Sales, and Product to share activation trends, feedback, and market intelligence that shape go-to-market strategy.

• 5+ years of experience in customer onboarding, activation, customer success, or implementation — preferably within SaaS, Fin Tech, or payments.

• Proven expertise in payments technology, workflows, and best practices
  , with the ability to consult at a strategic level.

• Exceptional communication and facilitation skills, including experience engaging with business owners, operations leaders, and financial decision-makers.

• Advanced problem-solving skills — with the ability to proactively identify adoption risks, design tailored solutions, and influence outcomes.

• Deep understanding of change management and how to guide customers through behavioral and operational shifts.

• A results-driven mindset — consistently meeting or exceeding activation, volume, and adoption KPIs.

• Highly collaborative and cross-functional — thrives on working with Sales, Product, and Support teams to deliver a seamless, high-impact customer experience.

• Deep subject-matter expertise in payments, including knowledge of processing platforms, merchant onboarding, and transaction lifecycle.

• Experience driving adoption of Stripe or similar payments solutions.

• A track record of transforming…